No, usually not. That would be like wasting money. Usually the other copy needs to stop working before I buy the same game twice.

Yes, I understood you perfectly. :-)
It seems like 95% of the things we learned at school went to waste. Geography, History, Biology, Chemestry, Philosophy, French... and for what? Would I miss a lot had I never heard about the Krebs cycle?

Due to knowledge inter-dependencies, acquiring skills, learning to learn and so on, we actually rely on a lot more than those 5% of things we recall learning.

I just stepped in because some people actually believe that 4 years is long enugh to get a proper education. I cannot leave that statement unoposed. No, kids, you're not too cool for school.
Now that I think of it, people who think like that don't usually hag around forums like this. :-S

Going back on track, if the games are cheap, I liked them and I would like to play them again, then I would consider repurchasing them on GOG. They get extra points if they bring some bonus content.

I do repurchase games but it's not as crazy as it sounds.

With the LucasArts games for instance, the only one that could be regarded as a 100% duplicate purchase was KOTOR.

With X-Wing and Tie-Fighter I have the stiffy based versions (which are probably unreadable by now), and I never had the expansions. And with Monkey Island, I had the original version, so the remake gives me an excuse to revisit this game as well.

But generally speaking, I do it for two reasons: I can get rid of the crack if the CD or DVD has copy protection, and it's easier to reinstall games from one installer file that I can just leave to run rather than having to hang around to feed a number of CDs or DVDs to the PC.